Twenty-eight letters, 11 June 1788–5 May 1812, written by members of the Green family, of Worcester, Massachusetts, include letters of Samuel Green (1767–1837), merchant, postmaster, and prominent resident of Columbia, S.C. from his days as a student in Rhode Island College [Brown University]. Sons of Dr. John Green (1736–1799) and Mary Ruggles Green (1741–1814), Samuel and his brother William Elijah Green (1777–1865) addressed frequent letters to their elder sibling Timothy Green (1765–1813), a 1786 graduate of Rhode Island College and practicing attorney in Worchester, Massachusetts, during their student days, usually reporting news from Providence, progress of their studies, and their continual need for funds. Letters from the 1790s include frequent references to the Greens' business interests in South Carolina, especially their involvement in the land speculation frenzy that swept the South. These letters complement the papers of Samuel Green already in the South Caroliniana Library.

Samuel commented, in a letter to Timothy written 11 February 1789, "We are studying Moral Phylosophy at present, [a subject] that has been lately introduced...." "I find it much more pleasing than I expected I should," he admitted. "The President call'd on me for money the other day, and said I must let him have some at the commencement of Vacation which will be the first of May; he said the Tutors would naturally expect some at that time," Samuel informed his brother.

Samuel Green left college before completing the requirements for his degree and by 1791 had moved to South Carolina to engage in the mercantile business in Columbia, S.C.; however, William Elijah Green, a younger brother, continued to rely on Timothy for funds for his education at Rhode Island College. "I should take it as a very great favor if you would send me some cash by the first opportunity of conveyance, for I am in very great want of it indeed," he pleaded in a letter of 20 May 1797. Three weeks later, on 13 June, William laid out his financial plight: "The Steward has, by the order of the President [Jonathan Maxcy] made out all the bills which are behind, & given them into the hands of Mr. Nicholas Brown the Treasurer [benefactor for whom the college was renamed in 1804] to collect," he related to Timothy.

After returning to Providence for the fall 1797 term, William, in a 23 October letter, confessed to Timothy that during his time at Rhode Island College, there had been too much company "to draw ones attention...." "If I had avoided [an active social life] on my first arrival here, I think I should have improved more in one year than I do now in three," he admitted. William also asked his brother if he could "afford to assist me in getting into Col. Burr's office to the study of Law." Of course, if he decided to leave Providence he would need "a sum sufficient to clear off in this town for I owe some considerable."

Even though Timothy enjoyed a very successful and lucrative law career in New York City, there were many demands on his resources in addition to the frequent requests from family members. He and his brother Samuel were early participants in many of the land speculation schemes that flourished in the 1790s. Timothy signed a purchase agreement on 1 November 1794 for 37,400 acres of land in Monongalia County, [West] Virginia, from a New York attorney, Joshua Mersereau (1728-1804), who represented the owners. Taking its name from the Monongahela River, the region originally known as Monongalia County was later carved into at least 13 counties in northern West Virginia, as well as portions of three others in western Pennsylvania. The land was represented as "being neither mountainous nor what is commonly called barrons and averaging one quarter bottom and ninety in a hundred good...land capable of being cultivated & made into a farm. In other respects to be under the same advantage of Inhabitants[,] deeds[,] covenants[,] courts of Law and danger from Indians...."

In a letter of 14 January 1797, Timothy instructed Eli Chandler in Philadelphia to purchase £10,000 "of Morrises paper Indorsed by Nicholson or Greenleaf?." Robert Morris, John Nicholson, and James Greenleaf had organized the North American Land Company in February 1795 and stock in the company rapidly plummeted in value before the company went bankrupt and Morris landed in prison in 1798. On the same day he wrote to Chandler, Timothy also sent a letter to Tennessee senator and fellow land speculator William Blount (1749-1800), explaining some of the difficulties in selling western lands. Apparently, a tract of land in Tennessee that he had previously been given the right to sell was being advertised by someone else. To Senator Blount he suggested, "perhaps it will be necessary to give me the copy of the Instructions to the agents in the business to prevent our destroying each others sales."

On 6 February 1797, Timothy wrote to his agent in Tennessee, Moses Fisk (1759-1843), who was in that area searching for available land and profitable trading locations. Timothy wanted to know "whether any large tract of good Lands can be bought on Duck river say 10000 acres of prime lands." "What is your opinion of Nashville as a place of Trade," he asked, "can I do any thing there[?]" "I wish to know if you know of any good situation on the Cumberland River for to lay out a small town?," he wrote. "I have a good number of young Merchants united for such an enterprise."

Samuel Green often traveled to New York to during the winter to visit with Timothy and to purchase "spring goods" to replenish his stock of merchandise in his Columbia store. He wrote Timothy on 21 May 1797 from Charleston where he had just arrived after "rather a long passage" of twelve days, the result of a head wind that had persisted for four days. Every thing, he wrote, "has quite a different appearance from NY." He observed, "half the people look as though it was a burden to them to carry their bodies about, it is so very warm." "String Beans, Cucumbers and Radishes are in great perfection as likewise Irish potatoes; they are much larger than an Egg," he noted. He also let Timothy know that he had delivered the papers "which your friend Colln. [Aaron] Burr sent by me...." Other current news involved Colonel Wade Hampton II (1754–1835) who "has gone with Major Butler in the State of Tennessee to endeavor to assist Major Butler to get security for a very valuable Tract of land sold to an agent of Govr. Blounts who failed in Philadelphia the last winter." As a final note, Samuel informed Timothy, "I shall this day visit the ashes of our dear departed Brother," a reference to Elijah Dix Green, who had died 21 September 1795 in Charleston, where he had practiced medicine for a short time after graduation from Rhode Island College in 1793.

Two letters from attorney Gardner Tufts in Savannah, Georgia, written in the spring of 1812 to "Dear Cousin" brought news to Timothy about the military state of affairs in Florida on the eve of the War of 1812. Tufts remarked in a letter of 28 March, "I have no doubt Florida including St. Augustine is in possession of this government...the last account stated the Revolutionist were to march against the fortifications on Fryday last - will drop you a Line on the pleasing news by next vessel." In his next letter, written from Savannah 25 May 1812, Tufts mentioned, "have no news from florida within a week." In both letters, Tufts wrote about the produce of his garden: "I will endeavor to procure you a few peach trees next fall...[and] some of the grape slips also - I have two very fine kinds in my garden," he wrote in March, and in May informed Timothy," having been told that green pease would keep by putting them in Bottles, I have sent you two Bottles of them...." "You will please apply for the pease on board the Brig Orozimba, Captn. Vail," he advised.

Letters to and from Timothy Green cease with the end of the year 1812. At the behest of his long-time friend Aaron Burr, Timothy had sailed to South Carolina in December 1812 to escort Theodosia, Burr's daughter, to New York for a visit with her father who had returned to the United States in July after four years of self-imposed exile in Europe. Burr had fled to Europe in 1808, soon after his acquittal on charges of treason, in order to avoid his numerous creditors and to escape the ire of his political enemies. Theodosia Burr Alston lived with her husband Joseph on their plantation near Georgetown, South Carolina, and it was from that port that Timothy Green and Theodosia sailed aboard the schooner Patriot on 30 December 1812. The vessel never arrived at New York and its fate still invites speculation. Several letters, already part of the Samuel Green collection, addressed to Samuel's sister-in-law, Mary Martin Green, document the family's grief after Timothy's loss at sea. Upon the receipt of a letter written by Mary on 13 February 1813, Samuel replied, on 4 March, "I have been under great apprehension for the fate of my poor Brother for some time...," but by early April when he wrote again, he had accepted the certainty of his brother's death. "You may be assured," he wrote to Mary on 3 April, "that my mind is almost borne down with affliction - My dear departed Brother I trust is at peace...."